EP2003172A1 - Indoliumverbindung und optisches aufzeichnungsmaterial - Google Patents

Indoliumverbindung und optisches aufzeichnungsmaterial Download PDF

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EP2003172A1
EP2003172A1 EP07739440A EP07739440A EP2003172A1 EP 2003172 A1 EP2003172 A1 EP 2003172A1 EP 07739440 A EP07739440 A EP 07739440A EP 07739440 A EP07739440 A EP 07739440A EP 2003172 A1 EP2003172 A1 EP 2003172A1
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group
carbon atoms
general formula
ring
optical recording
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EP2003172B1 (de
EP2003172A4 (de
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Toru Yano
Koichi Shigeno
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Adeka Corp
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Adeka Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/2467—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes azo-dyes
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
    • G11B7/2495—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds as anions

Definitions

  • the present invention relates to a novel indolium compound which is used mainly for an optical recording material and the like, and also relates to an optical recording material comprising the indolium compound.
  • the present invention relates to an optical recording material used for an optical recording medium, information being recorded thereon as information patterns by means of a laser and the like.
  • the present invention relates to an optical recording material used for an optical recording medium which is capable of high-density optical recording and reproduction by a laser and the like, the laser having emissions in ultraviolet and visible regions, and being of low energy.
  • optical recording media are in widespread use, generally due to its superior characteristics such as large recording capacities, noncontact recording or reproduction, and the like.
  • recording is carried out by focusing the laser light on a minute area of the recording layer to change properties of the optical recording layer, while reproduction is performed based on a difference in intensities of light reflected from the recorded area and non-recorded area.
  • Patent Document Nos. 1 to 6 report styrylindolium compounds.
  • Patent Document 7 reports a cyanine compound of a low decomposition temperature, which has a benzyl group introduced at the 3-position of the indole ring. It is thought that a compound which decomposes at a low temperature forms a recorded portion (pit) of an optical recording layer easily and is considered to adapt to a high-speed recording medium.
  • these materials have not shown satisfactory performance in terms of light stability and recording characteristics.
  • Patent Document No. 1 Japanese Patent Laid-Open Publication No. H11-34489 Patent Document No. 2: Japanese Patent Laid-Open Publication No. H11-170695 Patent Document No. 3: Japanese Patent Laid-Open Publication No. 2001-342366 Patent Document No. 4: Japanese Patent Laid-Open Publication No. 2002-206061 Patent Document No. 5: Japanese Patent Laid-Open Publication No. 2003-313447 Patent Document No. 6: Japanese Patent Laid-Open Publication No. 2003-321450 Patent Document No. 7: Japanese Patent Laid-Open Publication No. 2003-231359
  • an object of the present invention is to provide a novel indolium compound which has high light resistance and shows thermal decomposition behavior suitable for an application in high-speed optical recording, and to provide an optical recording material comprising the indolium compound.
  • the present inventors conducted diligent research and, as a result, found a novel indolium compound of a specific cationic structure which shows excellent thermal decomposition behavior as an optical recording material. This finding led to the present invention.
  • the present invention has accomplished the object by providing an indolium compound represented by the following general formula (I).
  • ring A represents a benzene or naphthalene ring
  • the ring B represents a 5- or 6-membered heterocyclic or an aromatic ring
  • Z represents an alkyl group having 1 to 8 carbon atoms which may be substituted with a halogen atom or may be interrupted by -O-, -CO-, -OCO-, or -COO-, a sulfonyl group having a hydrocarbyl group having 1 to 8 carbon atoms, a sulfinyl group having a hydrocarbyl group having 1 to 8 carbon atoms, an alkylamino group having an alkyl group having 1 to 8 carbon atoms, a dialkylamno group having alkyl groups having 1 to 8 carbon atoms, a cyano group, a nitro group, a hydroxyl group, or a halogen group
  • R 1 represents a group represented by the following general formula (II) or (II')
  • R 2
  • the bond between S and T is a double or triple bond;
  • S represents a carbon atom;
  • T represents a carbon, oxygen, or nitrogen atom;
  • x, y, and z represent 0 or 1;
  • R 5 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom, or an alkoxy group having 1 to 4 carbon atoms which may be substituted with a halogen atom;
  • R 6 , R 7 , and R 8 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom;
  • R 6 and R 8 may be linked together to form a ring structure;
  • the bond between S' and T' is a double bond;
  • S' represents a carbon atom;
  • T' represents a carbon, oxygen, or nitrogen atom;
  • R a to R i each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, where the methylene group of the alkyl group may be replaced by -O- or -CO-;
  • M represents Fe, Co, Ni, Ti, Cu, Zn, Zr, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, Pt, or Ir.
  • the present invention has accomplished the object by providing an optical recording material comprising at least one kind of the indolium compound, the optical recording material being used to form an optical recording layer of an optical recording medium which has an optical recording layer disposed on a substrate.
  • the present invention has accomplished the object by providing an optical recording medium comprising an optical recording layer disposed on a substrate, the recording layer comprising the optical recording material.
  • the indolium compound of the present invention and the optical recording material comprising the indolium compound will be described in detail based on preferable embodiments.
  • the indolium compound represented by the general formula (I) will be described.
  • the alkyl group having 1 to 8 carbon atoms represented by Z which is a substituent of the benzene or naphthalene ring represented by the ring A, may be substituted with a halogen group or interrupted by -O-, -CO-, -OCO-, or -COO-, the point of substitution by the halogen group and the point of interruption by -O-, -CO-, -OCO-, or -COO- being optional, including a case where -O-, -CO-, -OCO-, or -COO- is linked directly to the ring A.
  • the alkyl group having 1 to 8 carbon atoms includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, pentafluoroethyl, methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy,
  • the hydrocarbyl group having 1 to 8 carbon atoms, possessed by the sulfonyl or sulfinyl group which is represented by Z includes an alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, cyclohexylmethyl, 2-cyclohexylethyl, heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, and the like; an alkenyl group such as vinyl, 1-methylethen-1-yl, propen-1-yl, propen-2-yl, propen-3-yl, butene-1
  • alkyl group having 1 to 8 carbon atoms, possessed by the alkylamino or dialkylamide group which is represented by Z includes the same alkyl groups exemplified above; a halogen group represented by Z includes fluorine, chlorine, bromine, iodine, and the like.
  • the organic group having 1 to 30 carbon atoms and represented by R 2 including, for example, an alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, cyclohexylmethyl, 2-cyclohexylethyl, heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl,
  • the substituents include an alkyl group such as methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, and the like; an alkoxy group such as methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy
  • the 5-membered heterocyclic ring represented by the ring B includes a pyrrole, furan, thiophene, pyrazolidine, pyrazole, imidazole, imidazolidine, oxazole, isoxazole, isoxazolidine, thiazole, isothiazolidine rings, and the like;
  • the 6-membered ring represented by the ring B includes a piperazine, morpholine, thiomorpholine, urolidine, pyridine, pyrazine, pyrimidine, pyridazine, triazine rings, and the like.
  • the 5- or 6-membered ring represented by the ring B may be condensed with other rings or may be substituted, with examples including a quinoline, isoquinoline, indole, urolidine, benzothiophene, benzoxazole, benzotriazole, azulene, phthalimide rings, and the like.
  • the anion represented by An m- includes as a monovalent anion, a halide ion such as a chloride, bromide, iodide, fluoride ions, and the like; an inorganic anion such as a perchlorate, chlorate, thiocyanate, hexafluorophosphate, hexafluoroantimonate, tetrafluoroborate ions, and the like; an organic sulfonate ion such as a benzenesulfonate, toluenesulfonate, trifluoromethanesulfonate, diphenylamine-4-sulfonate, 2-amino-4-methyl-5-chlorobenzenesulfonate, and 2-amino-5-nitrobenzenesulfonate, and sulfonate ions described in Japanese Patent Laid-Open Publication No.
  • an organic phosphate-related ions such as an octyl phosphate, dodecyl phosphate, octadecyl phosphate, phenyl phosphate, nonylphenyl phosphate, 2,2'-methylenebis(4,6-di-tert-butylphenyl) phosphonate ions, and the like; a bistrifluoromethylsulfonylimide anion; a bisperfluorobutanesulfonylimide anion; a perfluoro-4-ethylcyclohexanesulfonate ion; a tetrakis(pentafluorophenyl)borate ion; and the like.
  • a divalent anion a benzenedisulfonate, naphthalenedisulfonate ions, and the like may be cited.
  • a quencher anion which can deactivate (quench) the active molecules in the exited state and anions of metallocene compounds such as ferrocene, ruthenocene, and the like which have an anionizable group such as a carboxylic acid, phosphonic acid, and sulfonic acid groups on the cyclopentadienyl group.
  • the quencher anion includes those represented by the following general formula (A) or (B), or formula (C) or (D), or anions described in Japanese Patent Laid-Open Publication Nos. S60-234892 , H5-43814 , H5-305770 , H6-239028 , H9-309886 , H9-323478 , H10-45767 , H11-208118 , 2000-168237 , 2002-201373 , 2002-206061 , and 2005-297407 ; Japanese Patent Application Publication No. H7-96334 ; International Publication No. WO/98/29257 , and the like:
  • R 9 and R 10 each independently represent a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a -SO 2 -G group, G representing an alkyl, aryl that may be substituted with a halogen atom, dialkylamino, diarylamino, piperidino, or morpholino groups; a and b each independently represent a number from 0 to 4; further, R 11 , R 12 , R 13 , and R 14 each independently represent an alkyl, alkylphenyl, alkoxyphenyl, or halogenated phenyl groups.
  • the alkyl group having 1 to 4 carbon atoms represented by R 5 to R 8 , includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, and the like;
  • the alkoxy group having 1 to 4 carbon atoms, represented by R 5 includes methyloxy, chloromethyloxy, trifluoromethyloxy, cyanomethyloxy, ethyloxy, dichloroethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, and the like.
  • the halogen atom represented by R 5 to R 8 includes fluorine, chlorine, bromine, and iodine.
  • the ring structure formed by linking of R 6 and R 8 includes a cyclopropane, cyclobutane, cyclopentane, cyclohexane, tetrahydropyran, piperidine, piperazine, pyrrolidine, morpholin, thiomorpholin, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, imidazole, oxazole, imidazolidine, pyrazolidine, isoxazolidine, isothiazolidine rings, and the like, where these rings may be condensed with other rings or may be substituted.
  • the 5-membered ring which may contain an heteroatom includes a cyclopentene, cyclopentadiene, imidazole, thiazole, pyrrazole, oxazole, isoxazole, thiophene, furan, pyrrole rings, and the like;
  • the 6-membered ring which may contain a heteroatom includes a benzene, pyridine, piperazine, piperidine, morpholin, pyrazine, pyrone, pyrrolidine rings, and the like.
  • the alkyl group having 1 to 4 carbon atoms, represented by R a to R i includes those exemplified in the description of the general formula (II); a group resulting from replacement of a methylene group of the alkyl group by -O- include methoxy, ethoxy, propyloxy, isopropyloxy, methoxymethyl, ethoxymethyl, 2-methoxyethyl, and the like; a group resulting from replacement of a methylene group of the alkyl group by -CO- includes acetyl, 1-carbonylethyl, acetylmethyl, 1-carbonylpropyl, 2-oxobutyl, 2-acetylethyl, 1-carbonylisopropyl, and the like.
  • the indolium compound of the present invention represented by the general formula (I), those represented by the following general formula (IV) or (V) are preferable because they are easy to synthesize and are very soluble in organic solvents.
  • the indolium compounds wherein the groups represented by R 3 and R 4 are alkyl groups having 1 to 8 carbon atoms, groups which link R 3 and R 4 together to form a 5- or 6-membered heterocyclic ring without a multiple bond, or groups which link with the benzene ring to which NR 3 R 4 is bonded to form a 5- or 6-membered ring, are preferable because their production costs are low and their molar absorption coefficients are large:
  • R 3 and R 4 each independently represent a hydrogen atom, an organic group having 1 to 30 carbon atoms, or a group represented by the general formula (III); R 3 and R 4 may be linked together to form a 5- or 6-membered heterocyclic ring without a multiple bond or may be linked with the benzene ring to which NR 3 R 4 is bonded to form a 5- or 6-membered ring;
  • X as a substituent, represents an alkyl group having 1 to 8 carbon atoms which may contain a halogen atom or a hydroxy group or may be interrupted by an ether bond or as a substituent, an alkoxy group having 1 to 8 carbon atoms which may contain a halogen atom or a hydroxy group or may be interrupted by an ether bond, or a hydroxy, nitro, cyano, or halogen group;
  • q represents an integer from 0 to 4; the ring A, Z, R 1 , R 2 , Y, An m- ,
  • ring C represents a 5-membered heterocyclic ring
  • the ring A, Z, R 1 , R 2 , Y, An m- , n, and p are the same as in the general formula (I).
  • the organic group having 1 to 30 carbon atoms represented by R 3 and R 4 , includes those exemplified in the description of the general formula (I).
  • the 5- or 6-membered heterocyclic ring without a multiple bond, formed by linking of R 3 and R 4 includes a pyrrolidine, imidazolidine, pyrazolidine, thiazolidine, isothiazolidine, oxazolidine, isoxazolidine, piperidine, piperazine, and morpholine rings.
  • the alkyl group having 1 to 8 carbon atoms which may possess a halogen atom or a hydroxy group, or which may be interrupted by an ether bond, includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, pentafluoroethyl, hydroxymethyl, 2-hydroxyethyl, 2-hydroxypropyl, 4-hydroxybutyl, 2-methoxyethyl, 2-
  • the alkoxy group having 1 to 8 carbon atoms which may possess a halogen atom or a hydroxy group, or which may be interrupted by an ether bond, includes methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tert-heptyloxy, n-octyloxy, isooctyloxy, tert-octyloxy, 2-ethylhexyloxy, chloromethyloxy, dichloromethyloxy, trichloromethyloxy, trifluoromethyloxy, pentafluoroethyloxy, 2-hydroxyethyloxy, 2-methyl
  • indolium compounds represented by the general formula (IV) those represented by the following general formula (VI) are more preferable because their production costs are low and their molar absorption coefficients are large:
  • indolium compounds represented by the general formula (V) those represented by the following general formula (VII) are more preferable because they are easy to synthesize and are very soluble in organic solvents:
  • X 1 represents an oxygen, sulfur, or selenium atom, or -NR 11 -
  • X 2 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxy, nitro, cyano, or halogen group
  • R 11 represents an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 20 carbon atoms
  • s represents an integer from 0 to 3
  • the ring A, Z, R 1 , R 2 , Y, An m- , n, and p are the same as in the general formula (I).
  • the alkyl group having 1 to 8 carbon atoms represented by X 2 and R 11 , includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, cyclohexylmethyl, cyclohexylethyl, heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, and the like;
  • the alkoxy group having 1 to 8 carbon atoms, represented by X 2 includes methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyl
  • the preferable specific examples of the indolium compound, represented by the general formula (I) of the present invention, include the following compound Nos. 1 to 85. It is noted that the following examples show only indolium cations, omitting anions.
  • the polymethine chain may have a resonance structure:
  • indolium compound of the present invention represented by the general formula (I)
  • optical isomers such as enatiomers, diastereomers, or a racemic mixture
  • having, as the chiral center, the chiral atom to which groups represented by R 1 and R 2 are bonded there are cases where optical isomers such as enatiomers, diastereomers, or a racemic mixture are present, having, as the chiral center, the chiral atom to which groups represented by R 1 and R 2 are bonded.
  • any optical isomer among these may be isolated and used as such or may be used as a mixture thereof.
  • the indolium compound of the present invention is not restricted by the method of manufacture.
  • it may be synthesized by a condensation reaction of a 2-methylindole derivative and an aromatic aldehyde derivative, followed by a salt exchange reaction.
  • the group containing a multiple bond may be introduced during the process of preparing an intermediate 2-methylindole derivative.
  • Methods for this include a method whereby a starting material, arylhydrazine derivative, is reacted with a 2-butanone derivative having the multiple bond group represented by the general formula (II) to form an indole ring, and a method whereby a halogenated derivative of the multiple bond group is reacted with an indole ring.
  • Y may be introduced by means of Y-D which can react with NH of the indole ring, where D represents a halogen group such as chlorine, bromine, iodine, and the like; a sulfonyloxy group such as phenylsulfonyloxy, 4-methylphenylsulfonyloxy, 4-chlorophenylsulfonyloxy, and the like.
  • D represents a halogen group such as chlorine, bromine, iodine, and the like
  • a sulfonyloxy group such as phenylsulfonyloxy, 4-methylphenylsulfonyloxy, 4-chlorophenylsulfonyloxy, and the like.
  • the 2-butanone derivative containing the multiple bond group represented by the general formula (II) may be obtained by a reaction of acetone and an aldehyde having the corresponding multiple bond group.
  • the indolium compound represented by the general formula (I) is used not only as an optical recording material, but also as an optical element such as a light absorber and the like contained in an optical filter; a synthetic intermediate for pharmaceuticals, agrochemicals, perfumes, dyes, and the like, and; a raw material for various polymers such as various functional materials.
  • the present invention is not limited in any way by these applications.
  • the optical recording material of the invention contains at least one kind of indolium compound represented by the general formula (I) of the invention. Further, the optical recording medium of the present invention is obtained by forming on a substrate an optical recording layer comprising the optical recording material.
  • the indolium compound of the present invention and, if necessary, various compounds described later are dissolved in an organic solvent to prepare the optical recording material as a solution, the organic solvent including a lower alcohol such as methanol, ethanol, and the like; an ether alcohol such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, butyl diglycol, and the like; a ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol, and the like; an ester such as ethyl acetate, butyl acetate, methoxyethyl acetate, and the like; an acrylic acid ester such as ethyl
  • the optical recording material is coated on the substrate by a wet coating method including spin coating, spraying, dipping, and the like. Methods such as vapor deposition, sputtering, and the like may also be used.
  • a wet coating method including spin coating, spraying, dipping, and the like. Methods such as vapor deposition, sputtering, and the like may also be used.
  • the organic solvent its amount used is preferably such that the content of the indolium compound becomes 0.1 to 10% by mass of the optical recording material of the present invention.
  • the optical recording layer is formed as a thin film and its suitable thickness is usually 0.001 to 10 ⁇ m, preferably 0.01 to 5 ⁇ m.
  • the content of the indolium compound of the present invention is preferably 10 to 100% by mass of the solid content contained in the optical recording material of the invention.
  • the optical recording layer is preferably formed in a manner such that the optical recording layer contains the indolium compound of the present invention in an amount of 50 to 100% by mass.
  • the optical recording material of the present invention more preferably contains the indolium compound of the present invention in an amount of 50 to 100% by mass based on the solid content contained in the optical recording material of the invention.
  • the solid content contained in the optical recording material of the invention refers to the components left after removing the components other than the solid content, namely, the solvent and the like, from the optical recording material.
  • the solid content in the optical recording material is preferably 0.01 to 100% by mass, more preferably 0.1 to 10% by mass.
  • the optical recording material of the invention may contain, according to necessity, a compound usually used for an optical recording layer such as azo compounds, phthalocyanines, oxonols, squarylium compounds, indoles, styryl compounds, porphyns, azlenium compounds, chroconicmethines, pyrilium compounds, thiopyrilium compounds, triarylmethanes, diphenylmethanes, tetrahydrocholines, indophenols, anthraquinones, naphthoquinones, xanthene compounds, thiazines, acridines, oxadines, spiropyrans, fluorenes, rhodamines, and the like; a resin such as polyethylene, polyester, polystyrene, polycarbonate, and the like; a surfactant; an antistatic agent; a lubricating agent; a fire, azo compounds, phthalocyanines, o
  • the optical recording material of the present invention may contain, as a quencher for the singlet oxygen and the like, an aromatic nitroso compound, an aminium compound, an iminium compound, a bisiminium compound, a transition metal chelate compound, and the like.
  • these various compounds are used in an amount of 0 to 50% by mass based on the solid content contained in the optical recording material of the present invention.
  • a diimmonium compound may be added to the optical recording material of the present invention. Addition of the diimmonium compound more effectively prevents the decrease with time in the residual rate of absorbance, observed in the optical recording medium of the present invention.
  • the immonium compound When the immonium compound is added, its content is preferably between 0 and 99% by mass, more preferably between 50 and 95% by mass, of the solid contained in the optical recording material.
  • the material used as the substrate on which such an optical recording layer is formed there is no particular restriction on the material used as the substrate on which such an optical recording layer is formed, provided that it is essentially transparent to the writing (recording) light and reading (reproducing) light, examples including resins such as polymethyl methacrylate, polyethylene terephthalate, polycarbonate, and the like; glass and the like. Further, its shape is optionally selected corresponding to the application, from a tape, drum, belt, disc, and the like.
  • a reflection film by a vapor deposition or sputtering method using gold, silver, aluminum, copper, and the like.
  • a protection layer may be formed using an acrylic resin, an ultraviolet curing resin, and the like.
  • the optical recording material of the present invention is suitable for an optical recording medium, which is recorded and reproduced by use of a semiconductor laser, especially for publicly known single-, double-, or multi-layer discs such as CD-R, DVD ⁇ R, HD-DVD-R, BD-R, and the like, each of a high-speed recording type.
  • Manufacturing Example Nos. 1 to 4 show examples of manufacture of indolium compound Nos. 1 to 3, and No. 73, each represented by the general formula (I). Further, the following Examples 1 to 4 show examples of preparation of optical recording materials comprising compound Nos. 1 to No. 3 and No. 73, each obtained in the Manufacturing Example Nos. 1 to 4, respectively. The Examples also show the manufacturing examples of the optical recording media Nos. 1 to 4 using the optical recording materials.
  • Comparative Examples 1 and 2 show examples of preparation of the comparative optical recording materials using indolium compounds having different structures from those represented by the general formula (I) and manufacturing examples of the comparative optical recording media No. 1 and No. 2 using the comparative optical recording materials.
  • indolium compound Nos. 1 to 3 and No. 73 were synthesized.
  • the compounds obtained were identified by 1 H-NMR analysis.
  • the analytical results of compound Nos. 1 to 3 are shown in [ Fig. 1] to [Fig. 3 ], respectively.
  • In [Table 1] are also shown the yields of the compounds obtained and the results of measurement of the characteristic values [light absorption properties of solutions ( ⁇ max and ⁇ at ⁇ max), decomposition point].
  • the decomposition point refers to the temperature in the differential thermal analysis performed at a heating rate of 10 °C /min., whereat the mass of the sample begins to decrease.
  • the indolium compound Nos. 1 to 3 obtained in the Manufacturing Examples 1 to 3 were each dissolved in 2,2,3,3-tetrafluoropropanol in a concentration of 1.0% by mass to obtain the optical recording materials as solutions.
  • the optical recording material was spin coated on a polycarbonate disc substrate of 12 cm diameter to form a 100 nm thick optical recording layer, the disc having been provided with a foundation layer (0.01 ⁇ m) by coating a titanium chelate compound (T-50: manufactured by Nippon Soda Co., Ltd.), followed by hydrolysis,.
  • T-50 titanium chelate compound manufactured by Nippon Soda Co., Ltd.
  • the comparative optical recording material was prepared and, using the comparative optical recording material, the comparative optical recording media No. 1 and No. 2 were obtained in a similar manner as in Examples 1 to 3.
  • the light resistance was evaluated of the optical recording media No. 1 to No. 3 obtained in Examples 1 to 3 and the comparative optical recording media No. 1 and No. 2 obtained in Comparative Examples 1 and 2.
  • each of the optical recording media was irradiated by light of 55,000 lux and after 50 hrs' and 100 hrs' irradiation, the residual rate of absorbance at ⁇ max in the UV spectrum relative to the absorbance before irradiation was measured. The results are shown in the following [Table 2].
  • the optical recording media comprising optical recording layers comprised of the optical recording materials of the present invention, exhibit high residual rates of absorbance, even after 100 hrs. of light irradiation.
  • the comparative recording media comprising comparative optical recording layers comprised of the comparative optical recording materials, showed a case of lowered residual rate of absorbance after 50 hrs. of irradiation and showed a significant fall in absorbance after 100 hrs. of irradiation. Thus the light resistance of the comparative optical recording materials was not good.
  • the present invention provides a novel indolium compound and an optical recording material comprising the indolium compound, which are suitable for formation of an optical recording layer of an optical recording medium.
  • the specific indolium compound of the present invention has a low decomposition temperature, resulting in a low heat accumulation property which suppresses the heat interference, and is also highly light resistant.
  • the indolium compound of the invention is suitable for forming an optical recording layer of an optical recording medium.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Indole Compounds (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP07739440A 2006-03-31 2007-03-23 Indoliumverbindung und optisches aufzeichnungsmaterial Expired - Fee Related EP2003172B1 (de)

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EP2003172B1 (de) 2012-06-06
WO2007114074A1 (ja) 2007-10-11
US20090296554A1 (en) 2009-12-03
EP2003172A4 (de) 2010-07-28
KR20090003237A (ko) 2009-01-09
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US8188297B2 (en) 2012-05-29
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